My recommendation would be head to Ironbridge, out towards Buildwas on the B4380 towards Shrewsbury, turn off at Cressage (left) then head towards Cound/Pitchford then Kenly and Longville, head back onto B4371 heading back to Much Wenlock then B4376 to Brosley and back down the hill into Ironbridge.
This (like many routes around here) was one of my training routes. It’ll take you along the flat valley floor through the Gorge and out into the Bumps, you’ll not hit the big bumps of Stretton but you will encounter some that will take you a bit of a spin to get up, not long just enough to stretch your legs, then you’ll hit the top of Wnelock Edge which in itself is spectacular for both views and climb up onto it, then heading back into Brosley before Ironbridge to finish the loop.
It’ll be about 50 miles, you can shorten it if you/your mate feels a bit off and easy head back to Much Wenlock after Cressage then back into Ironbridge.
Failing that a loop out from Ironbridge up towards the Wrekin, out along to Upton Magne and High Ercall then over to Harper Adams Collage and turn around and head back to Ironbridge along the lanes to Legommery and through Wellington and back to the Wrekin and back to Ironbridge.
This route will head along the flatter open fields of the Shropshire Plain and it’s rolling and open, a decent distance and not too tasking only the first climb out of Ironbridge to the Wrekin and visversa back upto the Wrekin and down the hill into Ironbridge again.
Carparking, Ironbridge has loads in Coalbrookdale..
HTH